Substitution Reactions


A substitution reaction is one in which an atom or functional group attached to a carbon in an organic compound is/are replaced by a different atom or functional group.
i.e: AB + CD ---> AC + BD

This is the only way that a halogen can be added to an alkane:
Substitution reaction : chlorination of methane
Substitution reaction : chlorination of methane

Here you can see that the chlorine is replacing a hydrogen in the methane to form methyl chloride.



In a reaction such as butane with chlorine, there are two things that can happen. The result will hydrochloric acid along with either be 1-chlorobutane or 2-chlorobutane depending on which carbon the chlorine attaches to:

1-chlorobutane
1-chlorobutane
2-chlorobutane
2-chlorobutane


Substitution reactions can also occur with benzene:
external image benz1.gif external image line_arrow_end.jpgexternal image 100px-Chlorobenzene2.svg.png
Benzene + Chlorine -----> Chlorobenzene



Another Example:
Ethane + Bromine ---> Bromoethane + Hydrogen Bromide
CH3CH3 + Br2 --------> CH3CH2Br + HBr

UV in sunlight is a catalyst for the reaction. The Hydrogen Bromide will turn moist blue litmus paper red.
Bromoethane can still react further, as the other H atoms can still be replaced - Dibromoethane, Tribromoethane and Tetrabromoethane can also be produced.
Chlorine will react with alkanes similarly (as in the other examples above).








Sources:
http://en.wikipedia.org/wiki/Substitution_reaction
http://www.campusrn2rn.com/video/2096231:Video:14621
http://www.chalkbored.com/lessons/chemistry-12/organic-synthesis-worksheet.pdf